Michael Saylor’s Financial Wizardry

Andrew Throuvalas

Michael Saylor’s Strategy (MSTR) has just crossed a jaw-dropping milestone: 500,000 BTC in its treasury. 

That’s half a million whole coins. Worth over CA$62 billion.

It begs the questions, how does the company continue buying so much?

There is in fact an answer—or rather, a strategy (sorry)—and today we’re breaking it down.

A note on the strategy

The Strategy playbook involves using low-interest debt instruments like convertible bonds and issuing preferred stock to raise capital, which is then deployed to buy Bitcoin. The strategy hinges on the belief that Bitcoin is a superior store of value and will continue to appreciate over time.

Some claim Saylor has discovered an “infinite money glitch,” in the sense that as Bitcoin’s price rises, Strategy’s stock value also increases, which enables more borrowing and more Bitcoin buys. Repeat ad infinitum.

The strategy is bold, creative, never-been-done-before and certainly not without risk. Yet others seem to be taking notice—and taking action. But before we reveal who, let’s dive into how exactly Saylor is pulling this off.

Saylor’s Strategy, Simplified

Since 2020, Saylor has been using a mix of financial wizardry to amass bitcoin. The result? A $5.3 billion buying spree in 2025 alone, pushing their total BTC holdings past 500,000 coins as of March 24.

Here’s a breakdown of their four key plays:

1. Selling MSTR stock (like ice cream on a hot day)

Instead of dumping shares all at once (which could tank the price), MSTR trickles them out when the stock is up – particularly when the company’s market cap surpasses the value of its BTC holdings. Proceeds are used to buy bitcoin.

2. Borrowing (with a twist)

Convertible bonds are Strategy’s secret sauce for leveraging debt into Bitcoin buys.

They allow MSTR to borrow money cheaply, and allow the bondholder to swap for MSTR stock at a set price–one higher than the market price of MSTR at the time the bond was offered.

Here’s the kicker: the bonds are extremely low-interest–sometimes even 0%.

While accretive, the market is usually only thirsty for these bonds when BTC is up. This often means Strategy can only raise money this way during local bitcoin tops.

That’s where the next two plays come in.

3. STRK: A reward jar for investors

STRK is Strategy’s dividend stock that pays out a little every year—say, 8 cents for every dollar. Plus, if the company does well (like the stock hitting $1,000), owners can trade it in for a piece of MSTR. Saylor sells STRK to get more money for Bitcoin buys while keeping holders happy with the dividends.

4. STRF: Borrow low, yield high

Ever borrow $10 hoping to turn it into $20? That’s Saylor’s move here. He takes loans with interest (like 10%) to buy Bitcoin, betting it’ll grow way more (say 20% or higher)*.

If BTC dips, they’ve got MSTR’s cash flow to cover loan payments. If it soars, shareholders reap the rewards. 

It’s a gutsy play, but if Bitcoin keeps climbing long term, Saylor stays winning.

The takeaway from all of this? Saylor is developing financial products for every appetite, from retail investors to hedge funds to State Street.

If there’s a way for Saylor and MSTR to acquire more bitcoin, you can bet they’re going to find it.


*Historically, Bitcoin has yielded 80% annually for the past ten years

Metaplanet’s $293 Million Bitcoin Haul

Over in Japan, Metaplanet is channeling its inner Saylor, boosting its BTC treasury to 3,350 coins—worth $293 million as of March 24. Their latest grab? 150 more BTC.

This Tokyo-based firm is on a tear, aiming for 10,000 BTC by year-end and 21,000 by 2026. 

Metaplanet is executing Saylor’s Strategies on a smaller scale, in a separate geography – the Tokyo Stock Exchange. This means MetaPlanet isn’t in direct competition with Strategy. As it turns out, it’s also one of the only companies to have outperformed Strategy last year. 

We’ll be keeping an eye on this company.

Gamestop (GME) and Atai Join the BTC Treasury Club

Gamestop (GME) – the world famous meme stock of 2021 – is now onboarding the BTC train. On Tuesday, the company’s board of directors unanimously greenlighted itself for future BTC purchases.

“The board has unanimously approved an update to its investment policy to add bitcoin as a treasury reserve asset,” the company stated.

The company currently holds US$4.75 billion in cash and plans to raise up to $1.3 billion through convertible senior notes to purchase Bitcoin.

Meanwhile, biotech firm Atai is dipping its toes into the Bitcoin waters with a modest $5 million buy. 

It’s small potatoes compared to Strategy’s half-million stack, but it’s another publicly traded company betting on BTC as a reserve asset.

These moves hint at a growing trend: more firms want a piece of the hardest money ever.

Stay humble,

Andrew

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